In recent years, why candidates from Massachusetts seem unpopular?

[Agonized-Statism]

Coincidence. Kennedy tried the impossible by unseating an incumbent president via primary and had the protest vote split with Jerry Brown, Dukakis was doing the impossible by running against Reagan's legacy, Kerry came extremely close, Warren's just a bad candidate who struggled to find a niche in a crowded field, Patrick came in waaaaaaay too late, Romney didn't tap into the demand for right wing populism enough, Tsongas was outshined by Clinton.

The 1980s-2000s were arguably a more conservative time than years before and since. The south became way more important as those states grew in population and economy and their values became dominant (especially during the immediate post-9/11 emotional freakout). Massachusetts didn't appeal to them. It stunk of old, dirty, out-of-touch New Dealers like the Kennedys and terrifying """"""""""""""leftists"""""""""""""" like that hippie who won it in '72. The craving then was for someone folksy and gut feeling-centric. The state didn't produce anyone like that at the time. The demand for cosmopolitanism might put it back on the map soon.